What If With Leslie Grandy

What if the most powerful thing a leader can say right now is, "I don't know"?

In this episode of What If?, Leslie Grandy sits down with Hortense le Gentil, executive leadership coach, speaker, and author of Aligned and The Unlocked Leader, to explore why the future of leadership requires something very different from the old superhero model.

For decades, leaders have been rewarded for projecting certainty. They were expected to have the answers, set the direction, stay composed, and absorb the pressure. But in a world moving faster than any one person can fully understand—especially as AI reshapes work, decisions, and expectations—that model is becoming impossible to sustain.

And maybe the real breakthrough begins when leaders stop pretending it is.

Together, Leslie and Hortense explore:

• Why the "superhero leader" model leaves leaders exhausted and teams disconnected
• How saying "I don't know" can build trust instead of weakening authority
• Why self-awareness is the foundation for more human leadership
• How fear, perfectionism, and old success patterns become leadership traps
• Why leaders must learn to invite their fears to the table without letting those fears lead
• How AI makes empathy, intuition, creativity, and emotional nuance more important—not less
• Why leaders need to stop competing with AI and start deepening the capabilities that make them human
• How to create environments where people feel safe enough to question, experiment, fail, and grow

Hortense offers a powerful reframe for this moment: leadership is not about being the smartest person in the room. It is about creating the conditions where others can contribute what they see, know, question, and imagine.

That starts with humility.

Not the passive kind. The courageous kind.

The kind that says: I do not have all the answers, and I am willing to learn with you.

Because in a world where change is constant and certainty is scarce, "I don't know" is not a weakness.

It may be the beginning of trust, creativity, and real transformation.

Reflection question: Where are you still trying to lead by having all the answers, when your team may need you to model the courage to learn?

What if the real advantage in the age of AI isn't getting answers faster—but knowing which questions are worth asking?

In this episode of What If?, Leslie Grandy sits down with Prapti Jha, design thinking and innovation consultant, co-founder of We Speak Innovation, and former design thinking catalyst at Ford Motor Company, to explore what happens when AI enters the world of human-centered design.

On the surface, AI looks like a powerful accelerator. It can synthesize research, generate personas, benchmark competitors, summarize markets, and prototype ideas at a speed that once seemed impossible.

But speed is not the same as insight.

And efficiency is not the same as understanding.

Together, Leslie and Prapti explore:

• Why human-centered design depends on real observation, context, and ambiguity
• How AI can support innovation without replacing the discipline of understanding real human behavior
• Why AI-generated personas are useful but dangerous when mistaken for actual human insight
• What organizations lose when they compress time for exploration and questioning
• Why innovation labs often fail when they are isolated from the rest of the organization
• How embedding "innovation catalysts" across teams can shift culture more effectively than separating innovation into a protected lab
• Why the skills once called "soft" are becoming the hardest and most important capabilities in the age of AI
• How organizations can assess AI maturity by asking employees what problems they are solving or what opportunities they are creating with AI

Prapti also introduces the idea that AI maturity is cultural, not just technical. Immature organizations use AI primarily to move faster. More mature organizations use AI as a collaborator—one that helps people challenge assumptions, surface contradictions, and make better decisions.

That distinction matters.

Because bad processes plus AI do not create innovation.

They create faster bad outcomes.

This conversation is a reminder that the human role in innovation is not disappearing. It is becoming more essential. AI can support research, synthesis, prototyping, and decision-making, but it cannot fully capture context, emotion, irrational behavior, or lived experience.

Human-centered design still begins with humans.

And in an AI-accelerated world, the advantage belongs to organizations that protect the time, curiosity, and courage required to ask whether the answer they received is actually the right one.

Reflection question: Are you using AI to get to answers faster—or to ask better questions about what truly matters?

What if entrepreneurship isn't always about starting from scratch—but seeing what an existing business could become?

In this episode of What If? With Leslie Grandy, I sit down with Jon Staenberg, general partner at Agate Hound Fund, the first fund of funds dedicated to search funds, also known as entrepreneurship through acquisition.

Jon has spent decades investing in people, businesses, and ideas. From venture capital to private equity to winemaking in Argentina, his career has been shaped by curiosity, pattern recognition, and a willingness to ask both sides of the entrepreneurial question:

What if it all goes wrong? And what if it works?

This conversation explores a different kind of entrepreneurial creativity. Not the creativity of inventing something from nothing, but the creativity of stepping into an existing company with employees, customers, habits, and history and seeing how it can be adapted, strengthened, and carried forward.

Together, Leslie and Jon explore:

• Why search funds are better understood as entrepreneurship through acquisition
• How acquiring and operating a profitable small business differs from venture-backed invention
• Why grit, tenacity, humility, and a clear "why" matter more than polish
• What Jon looks for when backing first-time CEOs
• Why immigrants, military veterans, and children of family business owners often bring the right temperament for this path
• How investors evaluate a searcher over time through coachability, humility, judgment, and persistence
• Why the coming generational handoff of baby boomer-owned businesses creates a powerful opportunity
• How AI-native operators can modernize "good, boring businesses" faster than legacy owners may be able to imagine

Jon also shares the story of how he unexpectedly became a winemaker after a long lunch in Argentina, and why selling his vineyard after 20 years is less an ending than a transition. The thread that remains is community: bringing people together, building trust, creating value, and knowing when to move toward the next thing.

This episode is a reminder that creativity is not limited to invention.

Sometimes the most creative act is recognizing untapped potential in something that already exists, then having the discipline, humility, and stamina to make it better.

Because transformation does not always begin with a blank page.

Sometimes it begins with a business that deserves a next chapter.

Reflection question: Are you overlooking the possibility inside what already exists because you're waiting for something entirely new?

In part two of Leslie Grandy's conversation with Mark Canlis, owner of Seattle's iconic Canlis restaurant, the discussion moves beyond hospitality into a bigger question: what happens to human connection, creativity, and emotional experience in a world increasingly shaped by technology?

In part one, Leslie and Mark explored legacy, ritual, culture, and hospitality as invitation. In this continuation, they go deeper into the emotional work of leadership and service, and why deeply human experiences may become even more valuable as AI becomes more embedded in our daily lives.

Mark does not see hospitality as performance. He sees it as relationship. That distinction changes everything.

Together, Leslie and Mark explore:

• Why service can be exhausting and restorative at the same time

• How emotional labor becomes meaningful when it connects to purpose

• Why guests often leave Canlis feeling "restored," even when they may not have the words to explain why

• How fine dining safeguards important emotional moments, from anniversaries to last meals with loved ones

• Why authentic connection, craft, and presence cannot simply be automated away

• How small business owners can build cultures where people bring their whole selves to work

• Why leaders must model vulnerability before asking it of others

• How play, creativity, and permission help people break free from organizational gravity

Mark also offers a powerful challenge to leaders: stop asking employees to perform humanity from a script. Instead, create an environment where people are trusted, known, and invited to care from who they truly are.

The conversation closes with a reflection on Creative Velocity and the conditions required for creativity to flourish at work. Leslie reframes velocity not as speed for speed's sake, but as momentum with direction: the ability to break free from the gravitational pull of fear, bias, control, and convention.

Because creativity does not thrive in cultures where people are merely told what to do.

It thrives where leaders lower the gravity.

Where people feel safe enough to try, fail, ask, play, and bring forward what only they can see.

And in a world where AI can automate more tasks, the most valuable experiences may be the ones that feel unmistakably human.

Reflection question: Are you creating a workplace where people feel controlled into performance, or invited into their full humanity?

What if your company isn't defined by what it delivers—but by the human experience it exists to create?

In this episode of What If?, Leslie Grandy sits down with Mark Canlis, owner of Seattle's iconic Canlis restaurant, for part one of a two-part conversation about creative leadership, legacy, hospitality, and culture.

For more than 75 years, Canlis has been one of America's most celebrated restaurants. But Mark does not describe the business first as fine dining, cuisine, service, or even customer experience.

He describes it as invitation.

An invitation to matter. An invitation to be seen. An invitation to turn toward one another.

That distinction becomes the heart of this conversation. Because when an organization understands what it is truly here to create, it can adapt without losing itself.

Together, Leslie and Mark explore:

• Why hospitality is not performance, but an invitation into relationship
• How legacy brands can evolve without becoming rigid or nostalgic
• Why constraints often become fuel for creativity
• How Canlis reimagined itself during the pandemic by asking what it meant to "turn toward" when traditional dining was impossible
• Why culture is built through ritual, vulnerability, humor, and shared story
• How employee experience shapes customer experience long before a guest sits down
• Why Mark does not train staff to follow scripts, but asks what kind of human they are hoping to become
• How rituals like the Canlis "Candy Awards," Christmas Eve toasts, open mic nights, shared meals, and playful traditions create trust inside the team

Mark challenges a common leadership impulse: to control behavior from the outside in. Instead of scripting hospitality, he starts with desire, humanity, and intrinsic motivation. What does the employee want? Who are they becoming? How can the restaurant help unlock that person?

That approach creates a culture where people are not merely executing service standards. They are trusted to create deeply personal, meaningful experiences for guests because they have first experienced belonging, vulnerability, and relationship with one another.

Because the invitation to the guest begins with the invitation to the team.

And in a world increasingly shaped by automation, monitoring, and efficiency, that kind of human-centered leadership may become more valuable than ever.

Reflection question: Are you building a culture that tells people what to do—or one that helps them become the kind of people who know how to care?

Next week: Part two continues the conversation with Mark Canlis into creativity, emotional labor, AI, and why deeply human experiences may matter even more in a technology-shaped future.

What if the real skill of working with AI isn't knowing what it can do—but knowing when you need to lead?

In this episode of What If?, Leslie Grandy sits down with Leonard Boussioux, assistant professor at the University of Washington's Foster School of Business and adjunct assistant professor at the UW Allen School of Computer Science and Engineering, to explore how humans can collaborate with AI to solve complex problems, build new ideas, and expand creative capacity.

Leo's work sits at the intersection of operations, machine learning, artificial intelligence, and creative problem solving. His research investigates how humans and AI can work together more effectively—and why simply adding AI to the process doesn't automatically produce better or more original outcomes.

Together, Leslie and Leo explore:

• Why AI can make people more creative—but may also reduce diversity of ideas if everyone gets the same "excellent" suggestions

• The difference between human-in-the-loop and AI-in-the-loop thinking

• Why there is no single formula for when humans should lead and when AI should take more of the exploratory role

• How students can build confidence, agency, and creative capacity by using AI to bring their own ideas to life

• Why "vibe coding" is more than a technical skill—it's a way to learn orchestration, judgment, and problem framing

• How AI-native students may enter the workforce with skills and expectations that leaders are not yet prepared to recognize

• Why organizations need AI champions, safe access to the best tools, and cultures that encourage knowledge sharing

• How education must evolve to teach not just AI literacy, but ethics, lifelong learning, metacognition, and leadership

Leo also shares how he designs his classroom as a kind of adventure—one where students don't just learn tools, but discover what they are capable of building. By asking students to create real products from their own ideas, he helps them move from anxiety about AI to a sense of creative agency.

But the conversation also surfaces a critical warning: AI often recombines what it already knows. It may give you good ideas, but it may give everyone else the same good ideas, too.

That means the human role is not disappearing.

It is becoming more important.

Because the future of human-AI collaboration won't be defined by who can generate the most ideas.

It will be defined by who can push beyond the obvious, recognize what matters, and steer the system toward something more original, useful, and human.

Reflection question: When you work with AI, are you letting it lead you toward the probable—or are you pushing it toward what only you can imagine?

What if the biggest opportunity with AI isn't doing more with less—but doing what wasn't possible before?

In this episode of What If?, Leslie Grandy sits down with Scott Ehrlich, Chief Innovation Officer and Head of Corporate Strategy at Sinclair Broadcast Group, to explore how media, technology, and business model innovation are changing as AI reshapes what can be created, personalized, distributed, and scaled.

Scott has spent his career navigating major platform shifts—from early OTT subscription services at RealNetworks to digital-first studios, streaming platforms, FAST channels, and AI-enabled media strategy. His perspective is grounded in a simple but powerful idea:

A strategy without leverage isn't really a strategy.

Today, the mechanics of making things are no longer the biggest constraint. Production is faster. Distribution is broader. AI can generate, iterate, and adapt at speeds that would have been impossible just a few years ago.

But that creates a new challenge.

When everything can be made, the real question becomes: What should exist at all?

Together, Leslie and Scott explore:

• Why value is shifting from production capability to judgment, relevance, and timing
• How AI changes the creative process by making iteration faster and less expensive
• Why personalized storytelling may become a new frontier for media innovation
• Why AI-native platforms may become the next operating systems for content discovery
• How business models must evolve when audiences consume information inside AI interfaces
• How leaders can drive adoption by focusing on one powerful promise: eliminating the toil of work

Scott also offers a grounded view of where most organizations are in the AI adoption curve. Before companies can transform workflows, they often need to use AI to improve existing ones. The breakthrough, he argues, starts with helping people remove the frustrating, repetitive work that drains their time and attention.

But the bigger opportunity is still ahead.

Too much of the current AI conversation is focused on efficiency: fewer people, fewer steps, faster processes. Scott challenges leaders to look beyond that and ask a more expansive question:

What new things can we do now that we could never do before?

Because the future of innovation won't belong only to those who move faster.

It will belong to those who can recognize where new leverage is forming—and use it to create something more meaningful.

Reflection question: Are you using AI only to streamline what already exists—or to imagine what could exist next?

What if culture isn't what your company says—but what your people actually experience when it matters most?

In this episode of What If?, Leslie Grandy sits down with Kelly Breslin Wright, veteran executive, former President and COO of Gong, and founder of Culture Driven Sales, to explore a leadership challenge that becomes impossible to ignore as organizations scale:

Misalignment.

As companies grow, what once felt clear and shared begins to fragment. Leaders use the same words—innovation, customer obsession, growth—but mean different things. Teams move in parallel, not together. And the gap between stated values and lived experience quietly widens.

Then AI enters the picture—and amplifies everything.

AI doesn't just accelerate work. It exposes inconsistencies. It surfaces where culture is unclear, where leadership signals are mixed, and where organizations say one thing—but reward another.

Together, Leslie and Kelly explore:

• Why culture is defined by what happens when people take risks, not what's written on the wall

• How to diagnose misalignment by asking a simple question: Does everyone describe our purpose the same way?

• Why companies often lose sight of their "why" as they scale—and what that costs them

• The critical role of leaders as "Chief Belief Officers" in aligning and inspiring teams

• How AI is leveling the playing field, making people and leadership the true differentiators

• Why psychological safety and honest conversations matter more in moments of disruption

• How to build cultures where experimentation is expected—and failure is not punished

• The risk of treating employees like outputs instead of humans—and how that erodes performance

Kelly also shares lessons from her early experience running a door-to-door sales business—where resilience, adaptability, and emotional intelligence weren't theoretical concepts, but daily survival skills. Those same capabilities, she argues, are now essential for navigating modern organizations.

Because while AI can increase speed, efficiency, and access to information, it cannot replace what great cultures create:

Belief, trust, and the willingness to take risks together.

This episode is a clear reminder that in a world where technology is advancing rapidly, the organizations that win won't just be the most technically capable.

They'll be the most aligned.

Reflection question: If you asked your leadership team to describe your company's purpose, would you hear one answer—or many?

What if the biggest risk to your career isn't AI—but waiting for someone else to decide your future?

In this episode of What If?, Leslie Grandy sits down with Dr. Cynthia Benson Mercer, human capital strategist, executive coach, and author of Human Capital Investment Strategy, to explore a fundamental shift happening inside organizations:

Agency is no longer optional. It's required.

As AI reshapes work—automating execution, accelerating analysis, and leveling access to information—the rules of value creation are changing. Effort alone is no longer enough. Titles are less stable. And the idea that "if I work hard, someone will notice" is quickly becoming outdated.

Instead, both individuals and organizations are being forced to rethink what human contribution actually means.

Together, Leslie and Cynthia explore:

• Why human capital should be treated as a compounding investment, not a cost center
• The critical difference between having value and articulating value
• Why employees must take ownership of their careers—rather than outsourcing it to managers or companies
• How to define your "aspirational next" and actively build toward it
• The danger of reducing people to roles, titles, or "boxes"—instead of seeing them as adaptable "puzzle pieces"
• What leaders get wrong about layoffs, talent mobility, and long-term workforce strategy
• Why transparency, communication, and intentionality matter most during disruption
• How AI is shifting value toward creativity, judgment, empathy, and complex problem-solving

Cynthia also offers a powerful reframe: every individual carries their own human capital—their skills, knowledge, and potential—and they have the agency to deploy it wherever it can create the most value. Organizations don't own that value. They invest in it—and must continuously earn the right to keep it.

This creates a new kind of tension.

Companies say people are their greatest asset. But how they hire, develop, move, and sometimes let go of those people reveals what they actually believe.

Because in a world where technology is advancing rapidly, the advantage doesn't go to those who simply adapt.

It goes to those who take ownership.

What if the biggest risk in your organization isn't moving too fast—but waiting too long?

In this episode of What If?, Leslie Grandy sits down with Sean Atkins, CEO of Dhar Mann Studios and a veteran media and technology leader whose career spans MTV, HBO, Discovery, Yahoo, and Disney—organizations that have all had to navigate massive industry shifts in real time.

Large organizations are built for execution. They scale what works. They reduce ambiguity. They optimize for predictability.

But in moments of transformation, those same strengths become constraints.

Because by the time something looks safe—your audience has already moved on.

This conversation explores what it actually takes to lead inside that tension.

Together, Leslie and Sean unpack:

• Why creative leadership isn't about having the best idea—but having the courage to act under uncertainty
• How to distinguish between trends and true behavioral shifts
• The three signals Sean uses to evaluate opportunities: velocity of adoption, business model clarity, and historical precedent
• Why waiting for certainty is often the most dangerous strategy in a changing market
• How curiosity becomes valuable only when paired with discernment and decision-making
• Why creativity exists in every function—from finance to operations—not just "creative roles"
• The hidden cost of homogeneous teams—and how diverse inputs drive better outcomes
• What it means to intentionally hire people who challenge culture—not just fit it

Sean also shares a candid look at what it's like to be a "maverick" inside large organizations—where leaders say they want disruption, but often resist the discomfort that comes with it. He reflects on the personal tradeoffs, the political realities, and the importance of learning how to navigate systems—not just challenge them.

The conversation also turns to AI, and the uncertainty it introduces. Rather than offering false clarity, Sean takes a pragmatic view: this is a moment of real disruption, real anxiety, and real opportunity—all at once.

Because the future won't be shaped by those who wait for the path to be clear.

It will be shaped by those willing to step into ambiguity—and learn faster than the system can resist them.

Reflection question: Where are you waiting for certainty—when the real opportunity requires you to move first?